Orthogonal Glycosylation with Phosphate Acceptors for Expeditious Synthesis of Bacterial Inner Core Oligosaccharides.
Chem Asian J
; 18(15): e202300424, 2023 Aug 01.
Article
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| MEDLINE
| ID: mdl-37339944
ABSTRACT
We report a practical one-pot glycosylation strategy for synthesis of bacterial inner core oligosaccharides that composed of unavailable L-glycero-D-manno and D-glycero-D-manno-heptopyranose components. The glycosylation method features a new orthogonal glycosylation procedure; whereby a phosphate acceptor is coupled with a thioglycosyl donor producing a disaccharide phosphate, which can be engaged in another orthogonal glycosylation procedure to couple with a thioglycosyl acceptor. The phosphate acceptors used in above one-pot procedure are directly prepared from thioglycosyl acceptors via the in-situ phosphorylation. Such phosphate acceptor preparation protocol eliminates the traditional protection and deprotection procedures. Based on the new one-pot glycosylation strategy, two partial inner core structures of Yersinia pestis lipopolysaccharide and Haemophilus ducreyi lipooligosaccharide were acquired.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Oligosacáridos
/
Fosfatos
Tipo de estudio:
Guideline
Idioma:
En
Revista:
Chem Asian J
Año:
2023
Tipo del documento:
Article
País de afiliación:
Taiwán